Title: Pittsfield Guest Houses from CA $1,224 | Expedia.ca [Pittsfield Travel Guide](https://expedia.ca/Pittsfield.dx184066)[Hotels in Pittsfield](https://expedia.ca/Pittsfield-Hotels.d184066.Travel-Guide-Hotels)[Vacation Rentals in Pittsfield](https://expedia.ca/Pittsfield-Vacation-Rentals.d184066.Travel-Guide-VacationRentals)[Flights to Pittsfield](https://expedia.ca/Cheap-Flights-To-Pittsfield.d184066.Travel-Guide-Flights)[Pittsfield Car Rentals](https://expedia.ca/Car-Rentals-In-Pittsfield.d184066.Car-Rental-Guide)[Pittsfield Vacation Packages](https://expedia.ca/Pittsfield.d184066.Destination-Travel-Guides) ![Default HTG hotel image](https://media.expedia.com/media/content/shared/images/travelguides/sem-hotels-tablet.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search Guest Houses in Pittsfield from CA $1,224 ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates Next weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=184066&startDate=2025-10-31&endDate=2025-11-02&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=184066&startDate=2025-11-07&endDate=2025-11-09&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=184066&startDate=2025-11-21&endDate=2025-11-23&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=184066&startDate=2025-12-19&endDate=2025-12-21&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Pittsfield Guest Houses ![Smart TV](https://images.trvl-media.com/lodging/112000000/111750000/111740100/111740098/f8fda1e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/111750000/111740100/111740098/1929f2bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor spa tub](https://images.trvl-media.com/lodging/112000000/111750000/111740100/111740098/w986h555x107y0-be91d3c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/112000000/111750000/111740100/111740098/50074a95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Slopeside Estate Guesthouse: Ski On/Off, Hot Tub, Views! Killington 10/10 Exceptional (2) CA $540 CA $1,224 total includes taxes & fees Oct 25 - Oct 26 [](https://www.expedia.ca/Killington-Hotels-The-Apartment-At-The-Slopeside-Estate-House-Ski-OnOff.h111740098.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-11-07&endDate=2025-11-08®ionId=184066&adults=2&lodging=GUEST_HOUSE&sort=RECOMMENDED&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FPittsfield-Guest-Houses.d184066-aaGuestHouses.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FPittsfield-Guest-Houses.d184066-aaGuestHouses.Travel-Guide-Accommodation) ## Top Pittsfield Hotel Reviews ![Après Inn Killington](//images.trvl-media.com/lodging/105000000/104900000/104893100/104893073/ae40488d_y.jpg) ### Après Inn Killington 10/10 Excellent "Wonderful location, beautiful renovations, friendly staff " [](https://expedia.ca/Apres-Inn-Killington.h104893073.Hotel-Information) ![Mountain Sports Inn](//images.trvl-media.com/lodging/2000000/1340000/1339900/1339833/7b3b252e_y.jpg) ### Mountain Sports Inn 10/10 Excellent "Piaf parking is my only complaint. Seems excessive " [](https://expedia.ca/Killington-Hotels-Mountain-Sports-Inn.h1339833.Hotel-Information) ![Greenbrier Inn](//images.trvl-media.com/lodging/2000000/1180000/1176800/1176792/e5569f51_y.jpg) ### Greenbrier Inn 10/10 Excellent "Didn't have breakfast so I can't comment. I got a sizable room and the setting was central to Killington activities and very quiet." [](https://expedia.ca/Killington-Hotels-Greenbrier-Inn.h1176792.Hotel-Information) ![The Mountain Inn at Killington](//images.trvl-media.com/lodging/1000000/980000/975400/975389/29356441_y.jpg) ### The Mountain Inn at Killington 10/10 Excellent "Friendly staff and extremely clean as always. " [](https://expedia.ca/Killington-Hotels-The-Mountain-Inn-At-Killington.h975389.Hotel-Information) ![Woodstock Inn & Resort](//images.trvl-media.com/lodging/1000000/30000/25700/25690/6bca8eff_y.jpg) ### Woodstock Inn & Resort 10/10 Excellent "Beautiful hotel with excellent staff and room cleanliness. Red Rooster Inn had good breakfast options, however dinner was a little underwhelming and expensive. There are better options at the local fine dining restaurants. " [](https://expedia.ca/Woodstock-Hotels-Woodstock-Inn-Resort.h25690.Hotel-Information) ![Killington Mountain Lodge, Tapestry Collection by Hilton](//images.trvl-media.com/lodging/1000000/110000/103700/103640/403a8548_y.jpg) ### Killington Mountain Lodge, Tapestry Collection by Hilton 10/10 Excellent "Great place to stay! The balcony was definitely nice to have as an option. The Mountain View were phenomenal. Highly recommend staying at this facility." [](https://expedia.ca/Killington-Hotels-Killington-Mountain-Lodge.h103640.Hotel-Information) ![North Star Lodge and Resort](//images.trvl-media.com/lodging/1000000/190000/185900/185873/0612ebf1_y.jpg) ### North Star Lodge and Resort 10/10 Excellent "We only stayed for one night, but I wish we had more time to enjoy the property. The sauna and older is small but very nice and easily accessible. Would love to come back in the winter." [](https://expedia.ca/Killington-Hotels-North-Star-Lodge-And-Resort.h185873.Hotel-Information) ![My Place Hotel-Randolph VT](//images.trvl-media.com/lodging/106000000/105670000/105665800/105665795/a55aa0fa_y.jpg) ### My Place Hotel-Randolph VT 10/10 Excellent "Clean quiet breakfast was great. We liked our first night so much we booked a second night. Highly recommend staying here." [](https://expedia.ca/My-Place-Hotel-Randolph-VT.h105665795.Hotel-Information) ![The Shire Woodstock](//images.trvl-media.com/lodging/11000000/10460000/10453700/10453651/3700fd69_y.jpg) ### The Shire Woodstock 10/10 Excellent "Our room was clean and welcoming. " [](https://expedia.ca/Woodstock-Hotels-The-Shire-Woodstock.h10453651.Hotel-Information) ## Find out more about Pittsfield ## Pittsfield Guest Houses information | Number of reviews | 2 | | --- | --- | | Accommodation | 5 Guest Houses | | Lowest Price | CA $1,224 | | Highest Price | CA $1,224 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [4 Star Hotels in Killington](https://www.expedia.ca/4Star-Killington-Hotels.s40-0-d10780.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Chittenden](https://www.expedia.ca/Chittenden-Hotels-Cheap-Hotels.0-0-d184042-tCheapHotels.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Chittenden](https://www.expedia.ca/Chittenden-Hotels-Luxury-Hotel.0-0-d184042-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Mountain Hotels in Chittenden](https://www.expedia.ca/Chittenden-Hotels-Mountain-Hotels.0-0-d184042-tMountainHotels.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Chittenden](https://www.expedia.ca/Chittenden-Hotels-Pet-Friendly-Hotel.0-0-d184042-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - 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